[M]y best [f]riend with long-distance-benefits gets curious about anal.

In case you haven’t read my older stories – My best friend and I wandered into sexting territory one bored night 2 years ago, kept coming back for more, finally met last December and consummated our long-distance-friendship-with-cross-country-benefits and are currently awaiting the next December before we get to meet again. Due to this once-a-year-for-just-one-month situation, we spend the majority of our time fucking each other with our words than our fun parts and making me write these stories on reddit is her way of adding some variety in the mix. If it gets her off, I’m more than happy to oblige.

For the most part, we’ve both been rather vanilla people. Some foreplay, guy-on-top, girl-on-top is routine, a little bit of doggy action with light spanking sprinkled on top if it’s an extra horny night. Complicated positions can get too wordy while sexting and mess with the flow, so we keep things simple. Except, the first time we had sex, I ended up cumming inside her and she gave me a rimjob. Once that dam was broken, for the past eight months, we’ve been slowly nudging each other into kinkier things each time we pick up the phone with our pants around our ankles.

The Adventures of Mad Bonney, Part I: The Stowaway [Bi, F21, F28, Rape discussed by characters, not depicted] [Historical Fiction/Pirates] [consensual]

AN: I did the first part as an answer to a prompt. Now I am writing a series of short stories following the evolution of these character’s sexual adventures. My partner, when I told him about the story, asked “Is it going to involve actual piracy at any point?” The answer is yes, but it’s more of a backdrop than a focus. If lesbian scenes aren’t to your tastes, just stick around for later parts. There will be MF, MFF, MM and MMFF. Something for everybody! 😅

~~

**Part I : The Stowaway**

The captain paced in the space of the cabin, eyeing the nibbled piece of hard tack on the table. She was waiting for the report on what was consuming their limited food supplies. Not ravenously, just the odd piece of tack here or there, perhaps a piece of dried fruit. Despite being a pirate, the captain loathed this sort of dishonesty. Pirates needed to work together. It just wasn’t done.

Soon the door to the cabin was shoved open, and the Master at Arms strode in, his brow furrowed deeply.

“We found the rat!” he muttered, staring down at his quarry.

Trading kinks with [m]y best [f]riend.

In case you haven’t read my older stories – My best friend and I wandered into sexting territory one bored night 2 years ago, kept coming back for more, finally met last December and consummated our long-distance-friendship-with-cross-country-benefits and are currently awaiting the next December before we get to meet again. Due to this once-a-year-for-just-one-month situation, we spend the majority of our time fucking each other with our words than our fun parts and making me write these stories on reddit is her way of adding some variety in the mix. If it gets her off, I’m more than happy to oblige.

For the most part, we’ve both been rather vanilla people. Some foreplay, guy-on-top, girl-on-top is routine, a little bit of doggy action with light spanking sprinkled on top if it’s an extra horny night. Complicated positions can get too wordy while sexting and mess with the flow, so we keep things simple. Except, the first time we had sex, I ended up cumming inside her and she gave me a rimjob. Once that dam was broken, for the past eight months, we’ve been slowly nudging each other into kinkier things each time we pick up the phone with our pants around our ankles.

“Wouldn’t it be hilarious if you pegged me?” [MF]

Men are so fucking weird.

I’ve had exactly one dude openly ask me to peg him without any awkwardness. Meanwhile, 4 men I dated have indeed wanted to be pegged.

I actually don’t blame men for this. I think there’s an unjustified stigma I will not be unpacking at this time. Anyway, it makes men feel weird about asking.

Anyway, onetime I was dating a dude who was a bit fascinated by my sexual history. He wasn’t even particularly jealous or weird about it, he just want to hear my stories.

Onetime we were sitting on the couch and in some show we were watching someone mentioned using a butt plug on her boyfriend.

“Oh my god, can you imagine doing that?”

I didn’t even bother looking up from my phone. “What? A butt plug?”

“Yeah! What does that even do?”

I shrugged. “It makes you feel good.”

“You’ve done it?”

“Yeah.”

“Like you’ve had a butt plug in or you’ve put one in a guy.”

Some of the best sex of my life was with a dude who was not particularly big [FM]

*I told y’all I’d write a companion piece to my tale of shitty sex with a dude who was huge.*

I’ve actually written about this guy in the past, but I never really mentioned this aspect specifically.

So I’ve said this before but I’m not sure y’all believe me: I’m not usually the hottest girl in a room. I’m not stupid in that I know I’m pretty. I’m blonde, cute, and have a nice body, but I’m an 8 who can pretty easily pull a 10 thanks to my energy.

All that is to say, I’m going to go out on a limb and assume I’m the hottest person this dude has ever fucked.

I’m not really sure what me and this dude were. He wasn’t exactly my friend but I fucked him on and off for like a year. He wasn’t particularly attractive, ambitious, or compatible with me on an emotional level. He was nice and cute enough, but conventional wisdom probably would not have put the two of us together.

*God, I sound like such a bitch writing this. I’m trying to be honest because it feels integral to the story.*

Free Use Slut/Escort to my Friend’s Dad – Part 5 [FM]

*Reposting from my previous delete profiles. As folks keep asking me for it.*

*By the end of first semester, dare I say it I was falling for him. I would have serviced him 7 days a week if he wanted me to. However, the weekly allowance, AP gifts and extra allowance after special events added a transactional feel to it all. It kept up just enough barriers. Probably for the both of us. We had already discussed and agreed to keep this going all of first year and the lease was extended. This happened right after finals. Prologue before finals.*

I finished worshiping and servicing his dick after about 20 minutes with my mouth. My hands were tied up behind my back. He held me down as he unloaded his sweet cum into my mouth and I eagerly swallowed it all. I kept him in my mouth as he lost his erection continuing to clean his dick. He kept running his fingers through my hair.

“You have finals soon don’t you whore?”

“Yes Daddy” I muffled out and nodded my head dick still in my mouth

He bent over spanked my ass a few times and undid my restraints. “Make out with me”

Free Use Slut/Escort to my Friend’s Dad – Part 3 [FM]

*Reposting from my previous delete profiles. As folks keep asking me for it.*

*I quickly fell into a routine after the first day. I sent him my course schedule and he worked around that once University started. I serviced him, with pleasure, 3 to 4 times a week. The sex was amazing. I had never been used by anyone like this before. It was rough. It was degrading. It was primal. Outside of sex things were normal and I genuinely enjoyed my time with him. My weekly allowance continued to arrive like clockwork.*

*I had started referring to him as Daddy by the time of the events below, as he was the dominant in our relationship. Please don’t think there was anything more to it.*

About six weeks in he invited me over to his condo on a Friday and asked me to sleepover. He was going to cook for me and told me to dress up.

I plugged my ass as instructed, put on a black corset and thong pair from Agent Provocateur, which he paid for, and a long black wrap dress. I imagined this is what his high end escorts wore to their “dates”. *I suppose I was an escort as well, I just had the one client*.

The worst sex of my life was with a man who had a very large penis [FM]

Jesus, I get asked about size so much from men who follow my account. I get why this is an insecurity, but I’m going to tell y’all a tale to set a few things straight.

*I’m writing this in two parts because I also fucked a very average-sized dude who made me climax into oblivion.*

Does size matter? Not in the way you think. I’m not going to lie, the two best male partners I’ve been with were quite large (my husband included). However, I don’t think their dick size made them magically good in bed. They were just confident and… um… creative.

I would also like to point out, one of my favorite sexual partners did not have a dick at all as she was, in fact, a girl. If anyone understands how little size matters, it’s queer girls. We don’t have a penetration obsession.

There has never ONCE been a time that a dude dropped his pants that I was like, “Oh man, that sucks.” You know why? Because I’m about to get fucked. All penises look good when they’re attached to someone I’m attracted to who is about to get freaky with me.

Big Stetch (M/F) (18+characters) (D/S)

Tears gathered at the corners of my eyes, threatening to spill. Grasping my wrists, one in each hand, Daddy tugged my arms back so that I was forced to arch into position. He told me to focus on keeping my chest down, so I did but my back cracked a bit, my first stretch of the day. His big hands dwarfed my wrists while I threw my weight against his restraint but he didn’t say another word so I just kept adjusting. I spread my knees as much as I could with my ankles secured by his Klein belt. It wasn’t very much. His silence told me he needed more from me. I knew what to do. With focus, I slowly worked on canting my hips and flaring my holes the way I knew he liked it. Pushing into the position slow and steady helped me adjust. It even felt good. It’s true I was horny for his cock, but I craved nothing like I did his approval. 

I [M30] went lingerie shipping with my married friend [F28] [mf]

We were 4 hours into a shopping trip at the centre and I was ready for home. Imogen had dragged me along with her under the premise that we’d grab coffee and put the world to rights like we used to.

Imogen was married, happily I think, but we’ve had our fun over the years too. She’s insatiable, I become a different person around her, it’s partly because she’s a flirt, partly because she’s got an amazing ass and I’m a sucker for it. We’ve never really spoken about it but there’s definitely an attraction there between us, I think I provide a little excitement as I’m the polar opposite of her husband. He’s vanilla, I’ve choked her before, he doesn’t like going down on her, I would have it for breakfast, he’s got an average dick, I’ve… Well….

Anyway the last stop was an expensive lingerie store, the king of awkward shops for a man, and I was very reluctant going in.

“Please Ryan, I trust your opinion, please.”

I couldn’t handle it when she pouted like that, begging.

“Ugh, okay.” I groaned. “But you owe me.”